Methanesulfonyl chloride → Methyl 2-(5,5-dimethyl-5'-(methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

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Reaction Steps

A solution of methyl 2-(5′-amino-5,5-dimethyl-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (307 mg, 0.958 mmol) in pyridine (15 ml) was cooled to 0° C. and methanesulfonyl chloride (0.090 ml, 1.150 mmol) was added; the reaction was warmed to room temperature and stirred for 25 minutes. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N HCl; the organic phase was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography on silica gel (DCM:MeOH from 99.5:0.5 to 98.75:1.25) affording methyl 2-(5,5-dimethyl-5′-(methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (351 mg, 0.881 mmol, 92% yield). MS/ESI+ 398.9 [MH]+.

Provenance & Evidence